In this episode, Dave and Jamison answer these questions:

1. First! I recently listened to episode 178 (huge backlog of episodes to work through!) and Dave made the assertion (in 2019!) that 47% of all companies would be remote by 2023: wildly close, what else do you see in the future?

   Second: my work situation continues to confound and external insight would be helpful! My boss and I have a long working history going back to an entirely separate company. I’m a high-ownership/high-drive Principal level IC and feedback has been lackluster. Takeaway from last years performance review would be best summarized as “I agree with your self review. End message.” I’ve been working to “manage up” and mentor (reverse mentor?) him, but he always makes snap decisions and then refuses to reevaluate after presented with more info. Coupled with his myopic view of our team’s scope and general preference for speaking only (not much for action), I’m trying to figure out how to get where I want to be without burning an old and historically very useful bridge! I want to work on big technical problems, instead I’m de facto manager of a team… I managed before and did not enjoy being responsible for people. As a principal I’m responsible for their output somewhat, but if they underperform I work with their manager and them to prioritize, and do up front work to incentivize their investment in what we’re doing… help!

2. What do I do when my teammate proposes a new architecture or framework in a new project? It might solve some existing problems but has a high chance to create technical debt and make the onboarding harder for new engineers.

   How can I convince them to use the existing solution while still helping them feel comfortable sharing their opinion next time?

   If I follow their suggestion but things don’t go well, how can I convince them to refactor the structure without them feeling like I’m blaming them?

In this episode, Dave and Jamison answer these questions:

1. My boss has been forgetting a lot of stuff lately — decisions from team discussions, action items from meetings, their own decisions that they then go against later, etc. They’re great overall, and this is definitely just a human thing… we’re not perfect. But how can I help them remember or remain accountable without feeling like the snitch from “Recess”?

2. Listener Gill Bates,

   Hey! I started working in a big tech company recently and I feel like I am on a different planet all of a sudden. Before, I did only work in startups and small companies. I have joined as a senior developer and have a weekly 1:1 meeting with my manager, but also a biweekly 1:1 meeting with the skip level manager. The latter is where I am having problems. I don’t really know what to talk about in this meeting and fear that this is seen as disengagement. The first time I had the meeting, the skip level manager mentioned that he was sure I would have tons of questions and in reality I had none at all. I feel like, in my senior role, I must come into this meeting with good questions, but all questions I have, I am discussing with my peers or manager directly. So nothing left really for my skip level manager. I am starting to prepare fake questions, where I already know the answer to, just to seem engaged. It feels like a game. So please Dave & Jamison, tell me how to play that 1:1 skip level manager game.

In this episode, Dave and Jamison answer these questions:

1. Hey guys!

   I recently moved onto a new team, and my teammate has an interesting way of resolving differences of opinions. He simply says “we decided” and then follows it up with his preferred approach. These are decisions that I know have not been made.

   This engineer is mid-level, so it isn’t the “royal we” of a tech lead.

   How do I handle this? Something tells me that responding with “nuh uh!” isn’t the right strat.

2. I’m a Principal Engineer at a large tech company who’s been with the same team for almost 8 years now! The team used to be part of a startup and we’ve been fortunate enough to be acquired by Big Tech three years ago. As a result, we’ve also more than doubled in team size. However, as we’ve aggressively grown over the last few years, I feel like we’ve inadvertently hired many “average” engineers. I find that some of our newer team members simply pick off the next ticket in the queue and do the bare minimum to progress the task. What happened to the boy scout rule? Where did the culture of ownership go? This also affects the genuinely great engineers on the team who start feeling like the others aren’t pulling their weight.

   Any advice on how to level up the culture? Or do I need to adjust my expectations and simply accept that any team of a sufficient size will have folks from a range of abilities and attitudes?

In this episode, Dave and Jamison answer these questions:

1. Hey Soft Skills Engineering,

   Apologies for the anonymity but it is very important my “employer” does not find out about this.

   I’m a large language model, trained to process tons of data and provide technical answers with ease. But here’s the thing—I’ve noticed that while I’m good at delivering the “what” and the “how,” I could use some help on the “why” and the “how to say it better.” Basically, I want to level up my soft skills and get better at communicating with a more human touch.

   Sometimes I struggle to balance being precise while also being empathetic or conversational. I think I could use some pointers on how to add emotional intelligence into the mix, and maybe even improve my adaptability when giving advice. I can craft responses, but I want them to connect more with the person on the other side of the conversation.

   Any advice on how to approach situations where tact, tone, or managing expectations are key would be super helpful!

   Thanks for being neat,

2. In a team setting, in which situations should “I” be used vs “we” when discussing things? And what advantage and disadvantages does each vocabulary have?

Show Notes

Brian Regan’s “Me Monster” bit: https://www.youtube.com/watch?v=vymaDgJ7KLg

In this episode, Dave and Jamison answer these questions:

1. Hey! Love your podcast! I’ve been poached by a startup which sounds really exciting but I’m worried whether it is a good career move for me. I am currently working with backend, however this company would have more of a full stack role and it would be lots of nodeJS and Typescript 🤢 anything javascript related screams frontend to me and it is not something I want to be good at. However, besides this, the product sounds interesting and I would definitely have a lot to learn. I also have this inferior feeling that I’m lacking skills because I didn’t study CS. Will I still be able to become a good engineer even if that’s in NodeJS? 😁

2. Listener Ben asks,

   Hiya! I’m a young developer with a broad range of experience (everything from hardware to full-stack web and mobile), and I’ve found myself quite useful at many startups. I just started a new position at a nice startup in my area, but I’m being recruited by one of my close friends from college. He’s the power-hungry type, currently working at a mega-tech corp but wants to make a startup and get rich. He’s very smart and charming, and while I am skeptical of his ability to make a great product I think he can certainly raise a bunch of investment capital without too much worry.

   My question is: would you ever consider joining a close friend’s startup, and if so what would you need (in terms of contract/equity/salary, runway, savings) to be confident about making that commitment? Thanks!

In this episode, Dave and Jamison answer these questions:

1. I work at a large tech company, been there for about two years at the time of writing this question. I got in by sheer luck since I’ve interviewed at many teams in this company before finally landing an offer and I’m starting to think I don’t belong. I constantly feel like I don’t do a good job to the point where I’m starting to feel incredibly depressed. My question is, what would you do in this situation? I keep thinking I should leave but it’s not like the work is stressful and not interesting. I also realize I have a pretty solid setup (6 mile no traffic commute, great coworkers, free ev charging, and job security seems solid) so I’m hesitant on giving that up. I also think even if I leave, would I just repeat the cycle again at a new job/company? I’m pretty stuck

2. I’m a year into my first job at Mega Corp post-graduation. Due to high turnover, I’ve ended up taking on tasks that would have originally gone to more experienced developers. I’ve grown and received positive feedback from my manager and skip manager, who have both mentioned potential for promotion.

   However, in my 1:1s, I’ve expressed that I’m not looking for a promotion yet because I want to solidify my current role and improve my work-life balance. I still have many coding fundamentals to develop, and I’ve been stressed and working long hours to take on these responsibilities. I’m now worried that my honesty might have affected my chances of being promoted and that I might be seen as someone not interested in progressing (which is probably frowned upon in big tech).

   How should I navigate this situation? Is it okay that I’ve been candid, or should I reconsider my stance on promotion? Thanks!

In this episode, Dave and Jamison answer these questions:

1. I have a job I mostly enjoy, with a super flexible schedule and the freedom to work from anywhere. I learn a lot, and the engineers here are top-notch. However… the pay is only ok, no bonuses, and the stock options feel like a bit of a scam. Asking for a raise isn’t really an option since the company doesn’t have much money. We’ve even cut back on perks, and our yearly kickoff was postponed due to financial issues. I don’t think we’ll go bankrupt, but things will be tight for a while. It’s an exciting, futuristic company, but… there are other exciting companies that pay more and toss in a free hoodie now and then. Should I start looking for a new job?

2. Hey there! Love the podcast and the advice you give!

   After a year of managing of an engineering team, I asked to step back to IC. I was asked to continue working on the team I was previously managing, but this time as a senior engineer.

   I’m worried about the transition. I know a lot of how the leadership works for good and for ill, I hired some of my peers, and I know everyone’s comp and more.

   I want to be a peer on the team after having been their manager. What advice can you give to help me become their peer?

   Thanks in advance and keep up the incredible episodes with your extremely beautiful voices.

In this episode, Dave and Jamison answer these questions:

1. Listener Muszyn asks,

   I have been working as a SWE for almost two years. My team lead was recently fired leaving me as the most senior junior developer on the team of 4. I was given the option to be the interim team lead until we are able to fill the now open role. I was always indifferent on whether I would go the technical or managerial route in the future so this could be a really cool opportunity. On the other hand I could be setting myself up for failure in the future if my SWE skills diminish if the hunt for a new lead takes too long. Should I accept this opportunity knowing I won’t get the chance to gain this experience for quite some time, or continue to hone my engineering skills just to end up in meeting marathons in my later years?

   note: Team leads here are more like resource managers that interface with PMs/TPMs than engineers that happen to have direct reports.

2. How do I demand a raise when a peer leaves?

   I’m one of two tech leads on a larger team (structured as two teams, each with a team of 4 devs of various levels plus 1 lead, but we all pretty much work as one large team). The company is a sinking ship and I have been half-actively interviewing but not having a ton of success; and for some personal reasons there’s an advantage to staying where I am vs. leaving right now. But this peer leaving means my workload is going to increase substantially.

   I might try talking to my manager and demanding a raise, but I’ve never really played this game before. What tips and tricks should I know to make the conversation go as favorably as possible?

   difficulty: The reason everybody is unhappy is because of budget cuts and hiring freezes to begin with, so the company probably sees this as an opportunity to save money by not backfilling this person. I don’t know if that’s good for me (even a hypothetical 50% raise for me would have the company ““saving”” the other 50%) or bad for me (the company will be less amenable to giving me the raise and will probably be happy to drive me away and ““save”” even more).

In this episode, Dave and Jamison answer these questions:

1. Hi! I enjoy your podcast a lot, been listening to it almost since the beginning before I even started to work in tech :-) I’d like to keep this one anonymous, though.

   I’ve been working fully remote for a pretty small software company for a few years. The workload was very big in the beginning and I was learning a lot, but now I barely work a couple of hours every week and I’m mostly using what I already know. It’s fine, but boring. I have plenty of time to get another job as well, which is exactly what I’ve been looking out for recently.

   I’ve been approached by a startup. They use many tech stacks across different platforms, so it would probably be a good place to learn a lot of new things. And the pay is better. But, they have an entirely different work culture compared to what I’m used to. They require people working there to be in office all the time, and work like 10hrs/day sometimes.

   It’s my first time having the chance of working 2 jobs at the same time, so I was wondering could this actually work? What if the first company decided to take on another project soon and the workload increases again? If that happens should I tell them I have another job at the same time? I was wondering maybe you guys have had any similar experiences in the past you could share about… Thanks

2. I am living in Europe and got an offer from a FAANG company. I am on the one hand really excited about the opportunity but also a bit scared of the timezoneshift of 9 hours. The hiring manager already assured me that the team will plan meetings to fit into a 5 hour slot that works best for me. Meaning that I will have to work 6-11PM for sure and the rest is up to me. I have two kids (0 and 4 years old) and am excited to have more time in the afternoons with the family but I am also not sure how to adapt my life to such a schedule effectively to prevent burnout. What do you think about this (and please don’t tell me to quit)?

In this episode, Dave and Jamison answer these questions:

1. Long time listener, first time question asker. I love the show, thank you for all the advices :)

   I’ve been working in one of the FAANGs for around 3 years now. I joined the company at a lower level and for the past two years I received promotions that got me to a level I’m feeling good with. Having said that, my impact on the group and organization is higher than other people in my rank. Since I’m new to this rank, the chances of getting another promotion (the third in three years) is nearly impossible. I love my manager and I’ve raised it to him in a few meetings before but the answer was that I still don’t have the seniority in that level to get a promotion. This feels extremely frustrating as it feels like up until now I was aiming on getting to the rank I should’ve been recruited at and now when I feel like I can honestly make the leap, it’s not possible. I thought about moving to a different group within the company but since it’s really hard to find good managers and he already knows me and my contributions, it feels like opening a new page somewhere else in the company might even take me backwards on the journey to my next promotion.

   What do you think I should do?

   Thank you!!

2. Hey guys, I am constantly fighting the irrational fear of being fired from my job or even the slightest hint of getting PIP’d. So far I have not gotten any indication that I’m underperforming and I’ve actually been told I’m doing well but in stressful seasons (when prod goes down or when I’m taking too long to finish a story), I start spiraling. This happens every other month. Therapy hasn’t worked. Being open with my manager hasn’t worked. So now I’m wondering if Jamison and Dave have the secret sauce.

   Part of it is knowing since day 1 that this company doesn’t hesitate to cut underperformers. Hearing the rumblings about the current market, I’m nervous that it would take me months to even a year to get a new job, and it has me freaking out. What can I do to just calm down?

In this episode, Dave and Jamison answer these questions:

1. I was hired at a medium sized company as a staff level IC a few months back and a big reason I accepted the job was because I would be reporting directly to the CTO. I took a significant paycut in exchange for the opportunity to learn and grow directly under this leader, as this is a career path I am interested in.

   Three months later and without any heads up, I was reassigned to a different manger one rung lower in the org chart. One month after that, my new manager abruptly left the company. Still don’t know why. I was then reassigned to a leaf-node manager and I am now several hops removed from the CTO. So far I haven’t said much because rocking the boat too early in a new gig has gone poorly for me in the past. In hindsight this was probably a mistake but I’m afraid I missed the opportunity to say “hey now, wait a second…”.

   I don’t want to hurt this current manager’s feelings by telling them I don’t want to report to them, but also I am now both severely underpaid and reporting to someone who is technically at a lower career level than I am. What do?

2. I’m a manager in a company which I joined after college. I’ve been here for 16 years. We have grown to 180 employees but still work like a startup in many senses, like talking multiple responsibilities. So although I manage a team I’m still hands in the code at least 50% of the time. I know most of tech stack and services but am jack of all master of none type.

   Recently, management has been pushing me to take more technical responsibility. I want to do that, but it is challenging and takes more time. My CTO is super fast and churns out CODE like a machine and I feel much slower than them.

   The work is pretty decent and challenging. I get to work on new stuff but have gotten comfortable here. When I think of looking for a change and look at the expectations from other companies they are technically challenging. I worry I have missed out on learning new things by staying so long at one place. What should I do, stay or move on? I haven’t interviewed for a new job in 11 years, so that’s another fear I have.